Porphyrins and tetraazaporphyrins are organic materials which have utility in a broad range of applications, such as pigments, laser dyes, photoconductors, optical recording media, and the like.
U.S. Pat. Nos. 4,061,654; 4,622,179; 4,731,312; 4,749,637; 4,766,054; 4,719,613; and 4,725,525 describe novel phthalocyanine and naphthalocyanine type dyes Which are adapted for application in optical recording systems.
U.S. Pat. No. 4,622,174 describes metallo-porphyrin complexes which are proposed for application in transparent protective laser shields.
U.S. Pat. No. 4,657,554 describes water-soluble azaphthalocyanines which are useful as photoactivators in textile bleaching operations.
J. Am. Chem. Soc., 106, 7404 (1984) by Wheeler et al describes the synthesis and characterization of bis(tri-n-hexylsiloxy)(2,3-phthalocyanato)silicon and its dimer.
Poly. Prepr. (Am. Soc., Div. Polym. Chem.) by Moyer et al describes the synthesis of monomeric silicon naphthalocyanine, and conducting cofacial polymers derived from the monomer.
U.S. Pat. No. 4,854,676 describes a bistable optical device comprising a Fabry-Perot etalon which has an optical cavity containing a naphthalocyanine dye medium as a nonlinear optical component.
There is a continuing interest in the development of new and improved porphyrin and tetraazaporphyrin type structures for specialized applications deriving from unique physicochemical and optical properties.
Other technology of background interest with respect to the present invention relates to the field of nonlinear optics which has potential for important applications in optical information processing, telecommunications and integrated optics.
Recently it has been recognized that organic and polymeric materials with large delocalized .pi.-electron systems can exhibit nonlinear optical response, which in many cases is a much larger response than by inorganic materials.
In addition, the properties of organic and polymeric materials can be varied to optimize other desirable properties, such as mechanical and thermooxidative stability and high laser damage thresholds, with preservation of the electronic interactions responsible for nonlinear optical effects.
Thin films of organic or polymeric materials with large second order nonlinearities in combination with silicon-based electronic circuitry have potential as systems for laser modulation and deflection, information control in optical circuitry, and the like.
Other novel processes occurring through third order nonlinearity such as degenerate four-wave mixing, whereby real-time processing of optical fields occurs, have potential utility in such diverse fields as optical communications and integrated circuit fabrication.
Of particular importance for conjugated organic systems is the fact that the origin of the nonlinear effects is the polarization of the .pi.-electron cloud as opposed to displacement or rearrangement of nuclear coordinates found in inorganic materials.
There is increasing research effort to develop new nonlinear optical organic systems for prospective novel phenomena and devices adapted for information control in optical circuitry, and for light valves and optical switches. The potential utility of organic materials with large second order and third order nonlinearities for very high frequency application contrasts with the bandwidth limitations of conventional inorganic electrooptic materials.
Accordingly, it is an object of this invention to provide polymerizable tetraazaporphyrin compounds which exhibit a novel combination of physical and optical properties.
It is another object of this invention to provide a thin film medium consisting of a tetraazaporphyrin polymer which exhibits nonlinear optical response.
It is a further object of this invention to provide a waveguiding optical medium for light modulation, comprising a thin film of a novel phthalocyanine and/or naphthalocyanine containing polymer.
Other objects and advantages of the present invention shall become apparent from the accompanying description and examples.